UA64752C2 - Нестероїдні (гетеро)циклічно заміщені ациланіліди з змішаною гестагенною та андрогенною активністю - Google Patents
Нестероїдні (гетеро)циклічно заміщені ациланіліди з змішаною гестагенною та андрогенною активністю Download PDFInfo
- Publication number
- UA64752C2 UA64752C2 UA99127245A UA99127245A UA64752C2 UA 64752 C2 UA64752 C2 UA 64752C2 UA 99127245 A UA99127245 A UA 99127245A UA 99127245 A UA99127245 A UA 99127245A UA 64752 C2 UA64752 C2 UA 64752C2
- Authority
- UA
- Ukraine
- Prior art keywords
- chz
- hydroxy
- methyl
- racemate
- phthalide
- Prior art date
Links
- 239000000583 progesterone congener Substances 0.000 title abstract description 14
- 230000000694 effects Effects 0.000 title abstract description 6
- 239000003098 androgen Substances 0.000 title abstract description 5
- 125000005842 heteroatom Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 148
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 30
- 125000005843 halogen group Chemical group 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000004185 ester group Chemical group 0.000 claims abstract description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 193
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 157
- -1 2-hydroxy-4-(2-methoxyphenyl)-4-methyl-2-trifluoromethylvaleroylamino Chemical group 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 229910052796 boron Inorganic materials 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 230000003993 interaction Effects 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229910052770 Uranium Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- MIWUNJGJUSWHTO-UHFFFAOYSA-N 2-hydroxy-2,4-dimethyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-4-phenylpentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(C)(O)CC(C)(C)C1=CC=CC=C1 MIWUNJGJUSWHTO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- PLCAABVVJJBUAK-UHFFFAOYSA-N n-(4-bromo-1-oxo-3h-2-benzofuran-5-yl)-2-hydroxy-4-methyl-4-phenyl-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=C(Br)C=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 PLCAABVVJJBUAK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- PLVFZQGMURDXFJ-UHFFFAOYSA-N 2-hydroxy-4,4-dimethyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)hex-5-enamide Chemical compound C=CC(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C2C(=O)OCC2=C1 PLVFZQGMURDXFJ-UHFFFAOYSA-N 0.000 claims description 3
- XQWVCRMHQFWIJK-UHFFFAOYSA-N 2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(1,1,2,2,2-pentafluoroethyl)-4-phenylpentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)C(F)(F)F)CC(C)(C)C1=CC=CC=C1 XQWVCRMHQFWIJK-UHFFFAOYSA-N 0.000 claims description 3
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-pentanol Substances CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 3
- ULPOSDMVRAOCKS-UHFFFAOYSA-N 4-ethyl-6-[[2-hydroxy-4-phenyl-2-(trifluoromethyl)pentyl]amino]-2,3-benzoxazin-1-one Chemical compound C1=C2C(CC)=NOC(=O)C2=CC=C1NCC(O)(C(F)(F)F)CC(C)C1=CC=CC=C1 ULPOSDMVRAOCKS-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- RRLLTJYTLKIFIA-UHFFFAOYSA-N 2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-4-phenyl-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 RRLLTJYTLKIFIA-UHFFFAOYSA-N 0.000 claims description 2
- 239000007818 Grignard reagent Substances 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000004673 fluoride salts Chemical group 0.000 claims description 2
- 150000004795 grignard reagents Chemical class 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 101100231508 Caenorhabditis elegans ceh-5 gene Proteins 0.000 claims 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
- GKOISAITVMDQGW-UHFFFAOYSA-N 2-hydroxy-4-methyl-n-[1-oxo-4-(trifluoromethyl)-2,3-benzoxazin-6-yl]-4-phenyl-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C(C(ON=C2C(F)(F)F)=O)C2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 GKOISAITVMDQGW-UHFFFAOYSA-N 0.000 claims 1
- ONELJVXCVDDQRX-UHFFFAOYSA-N 5-[[2-hydroxy-4-methyl-4-phenyl-2-(trifluoromethyl)pentyl]amino]-3h-2-benzofuran-1-one Chemical compound C=1C=C2C(=O)OCC2=CC=1NCC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 ONELJVXCVDDQRX-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 101150078171 OSH3 gene Proteins 0.000 claims 1
- 241000269435 Rana <genus> Species 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 27
- 239000000262 estrogen Substances 0.000 abstract description 9
- 239000003433 contraceptive agent Substances 0.000 abstract description 5
- 230000035558 fertility Effects 0.000 abstract description 5
- 230000002254 contraceptive effect Effects 0.000 abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
- 201000009273 Endometriosis Diseases 0.000 abstract description 2
- 230000003637 steroidlike Effects 0.000 abstract description 2
- 238000006467 substitution reaction Methods 0.000 abstract description 2
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 230000002175 menstrual effect Effects 0.000 abstract 1
- 208000011580 syndromic disease Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 165
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000012071 phase Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 14
- 230000000757 progestagenic effect Effects 0.000 description 14
- BWWXMPLQHHWEJJ-UHFFFAOYSA-N n-(4-bromo-1-oxo-3h-2-benzofuran-5-yl)-4-methyl-2-oxo-4-phenylpentanamide Chemical compound C=1C=C2C(=O)OCC2=C(Br)C=1NC(=O)C(=O)CC(C)(C)C1=CC=CC=C1 BWWXMPLQHHWEJJ-UHFFFAOYSA-N 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 230000001548 androgenic effect Effects 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- ISMUWQMUWFPFBZ-UHFFFAOYSA-N 5-amino-3h-2-benzofuran-1-one Chemical compound NC1=CC=C2C(=O)OCC2=C1 ISMUWQMUWFPFBZ-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- QWHVQTQEOKGYQN-UHFFFAOYSA-N 2-oxo-3-(1-phenylcyclobutyl)propanoic acid Chemical compound C=1C=CC=CC=1C1(CC(=O)C(=O)O)CCC1 QWHVQTQEOKGYQN-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 229940011871 estrogen Drugs 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- UCBIAWCJKKOAHL-UHFFFAOYSA-N 2-hydroxy-4-phenyl-2-(trifluoromethyl)pentanoic acid Chemical compound OC(=O)C(O)(C(F)(F)F)CC(C)C1=CC=CC=C1 UCBIAWCJKKOAHL-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229940095055 progestogen systemic hormonal contraceptives Drugs 0.000 description 5
- 239000012047 saturated solution Substances 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 5
- BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 description 4
- XSJPLFYKYMURJY-UHFFFAOYSA-N 4,4-dimethyl-2-oxohex-5-enoic acid Chemical compound C=CC(C)(C)CC(=O)C(O)=O XSJPLFYKYMURJY-UHFFFAOYSA-N 0.000 description 4
- ZQHDMZVMPFNTGG-UHFFFAOYSA-N 5-amino-4-bromo-3h-2-benzofuran-1-one Chemical compound NC1=CC=C2C(=O)OCC2=C1Br ZQHDMZVMPFNTGG-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229960002568 ethinylestradiol Drugs 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XAHRAWVICALETE-UHFFFAOYSA-N 2-oxo-3-(1-phenylcyclohexyl)propanoic acid Chemical compound C=1C=CC=CC=1C1(CC(=O)C(=O)O)CCCCC1 XAHRAWVICALETE-UHFFFAOYSA-N 0.000 description 3
- FWFKZBPRWVSXBK-UHFFFAOYSA-N 4-(3-methoxyphenyl)-4-methyl-2-oxopentanoic acid Chemical compound COC1=CC=CC(C(C)(C)CC(=O)C(O)=O)=C1 FWFKZBPRWVSXBK-UHFFFAOYSA-N 0.000 description 3
- KRRATTKMDZQNGX-UHFFFAOYSA-N 4-(4-iodo-2-methoxyphenyl)-4-methyl-2-oxopentanoic acid Chemical compound COC1=CC(I)=CC=C1C(C)(C)CC(=O)C(O)=O KRRATTKMDZQNGX-UHFFFAOYSA-N 0.000 description 3
- CYZBQOCHXKDBOA-UHFFFAOYSA-N 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic acid Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(O)=O)C(F)(F)F CYZBQOCHXKDBOA-UHFFFAOYSA-N 0.000 description 3
- FRUVVVPJVUXQTL-UHFFFAOYSA-N 4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-oxopentanoic acid Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(=O)C(O)=O FRUVVVPJVUXQTL-UHFFFAOYSA-N 0.000 description 3
- JQFGKPKESVXEOM-UHFFFAOYSA-N 4-methyl-2-oxo-4-phenylpentanoic acid Chemical compound OC(=O)C(=O)CC(C)(C)C1=CC=CC=C1 JQFGKPKESVXEOM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 102100032187 Androgen receptor Human genes 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 108010080146 androgen receptors Proteins 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 230000002860 competitive effect Effects 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 230000001076 estrogenic effect Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 239000013558 reference substance Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229960003484 testosterone enanthate Drugs 0.000 description 3
- VOCBWIIFXDYGNZ-IXKNJLPQSA-N testosterone enanthate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCC)[C@@]1(C)CC2 VOCBWIIFXDYGNZ-IXKNJLPQSA-N 0.000 description 3
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- MNAGFAFUEYEGAO-UHFFFAOYSA-N 2-(2-phenylpropyl)-2-(trifluoromethyl)oxirane Chemical compound C=1C=CC=CC=1C(C)CC1(C(F)(F)F)CO1 MNAGFAFUEYEGAO-UHFFFAOYSA-N 0.000 description 2
- CEXGTXNIIFSPSF-UHFFFAOYSA-N 2-bromo-4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1Br CEXGTXNIIFSPSF-UHFFFAOYSA-N 0.000 description 2
- HNQJOUFHXZSEQK-UHFFFAOYSA-N 2-hydroxy-4-methyl-2-(trifluoromethyl)pent-4-enoic acid Chemical compound CC(=C)CC(O)(C(O)=O)C(F)(F)F HNQJOUFHXZSEQK-UHFFFAOYSA-N 0.000 description 2
- SZUYDMXQRZFCLL-UHFFFAOYSA-N 2-hydroxy-4-methyl-4-thiophen-2-yl-2-(trifluoromethyl)pentanoic acid Chemical compound OC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CS1 SZUYDMXQRZFCLL-UHFFFAOYSA-N 0.000 description 2
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 2
- HSJFZYIUNSAMES-UHFFFAOYSA-N 2-oxo-3-(1-phenylcyclopentyl)propanoic acid Chemical compound C=1C=CC=CC=1C1(CC(=O)C(=O)O)CCCC1 HSJFZYIUNSAMES-UHFFFAOYSA-N 0.000 description 2
- JRGBQNMHOKJNTD-UHFFFAOYSA-N 2-oxo-3-(1-phenylcyclopropyl)propanoic acid Chemical compound C=1C=CC=CC=1C1(CC(=O)C(=O)O)CC1 JRGBQNMHOKJNTD-UHFFFAOYSA-N 0.000 description 2
- ZGRVTLLGLKMPAH-UHFFFAOYSA-N 2-oxo-4-phenylpentanoic acid Chemical compound OC(=O)C(=O)CC(C)C1=CC=CC=C1 ZGRVTLLGLKMPAH-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- VNWDGLDUNXNVIV-UHFFFAOYSA-N 2-trimethylsilyloxyprop-2-enoic acid Chemical compound C[Si](C)(C)OC(=C)C(O)=O VNWDGLDUNXNVIV-UHFFFAOYSA-N 0.000 description 2
- GVDJEHMDNREMFA-UHFFFAOYSA-N 3,3,3-trifluoro-2-oxopropanoic acid Chemical compound OC(=O)C(=O)C(F)(F)F GVDJEHMDNREMFA-UHFFFAOYSA-N 0.000 description 2
- FYYOTZLMLLTWAP-UHFFFAOYSA-N 3,3-dimethylpent-4-enoic acid Chemical compound C=CC(C)(C)CC(O)=O FYYOTZLMLLTWAP-UHFFFAOYSA-N 0.000 description 2
- OEIOKPQWHXSUCH-UHFFFAOYSA-N 3-amino-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(N)OC(=O)C2=C1 OEIOKPQWHXSUCH-UHFFFAOYSA-N 0.000 description 2
- MUFKYUFKPCKWFQ-UHFFFAOYSA-N 4,4-dimethyl-2-oxo-n-(1-oxo-3h-2-benzofuran-5-yl)hex-5-enamide Chemical compound C=CC(C)(C)CC(=O)C(=O)NC1=CC=C2C(=O)OCC2=C1 MUFKYUFKPCKWFQ-UHFFFAOYSA-N 0.000 description 2
- VKPRSAWGFXHIEO-UHFFFAOYSA-N 4-(4-ethenylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic acid Chemical compound OC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(C=C)C=C1 VKPRSAWGFXHIEO-UHFFFAOYSA-N 0.000 description 2
- NXUSSDJXYUWARA-UHFFFAOYSA-N 4-(4-iodophenyl)-4-methyl-2-oxopentanoic acid Chemical compound OC(=O)C(=O)CC(C)(C)C1=CC=C(I)C=C1 NXUSSDJXYUWARA-UHFFFAOYSA-N 0.000 description 2
- AQBXIOGPHBWBFP-UHFFFAOYSA-N 4-amino-2-bromobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(Br)=C1 AQBXIOGPHBWBFP-UHFFFAOYSA-N 0.000 description 2
- NJSMRVDMPNDTDC-UHFFFAOYSA-N 4-phenyl-2-(trifluoromethyl)pentane-1,2-diol Chemical compound OCC(O)(C(F)(F)F)CC(C)C1=CC=CC=C1 NJSMRVDMPNDTDC-UHFFFAOYSA-N 0.000 description 2
- AUIQUSQXFBHMMZ-UHFFFAOYSA-N 5-(2,5-dimethylpyrrol-1-yl)-3-prop-1-enyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(C=CC)OC(=O)C2=CC=C1N1C(C)=CC=C1C AUIQUSQXFBHMMZ-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 206010054834 Hypergonadism Diseases 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- HGXJOXHYPGNVNK-UHFFFAOYSA-N butane;ethenoxyethane;tin Chemical compound CCCC[Sn](CCCC)(CCCC)C(=C)OCC HGXJOXHYPGNVNK-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 210000000172 cytosol Anatomy 0.000 description 2
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002084 enol ethers Chemical class 0.000 description 2
- 229960005309 estradiol Drugs 0.000 description 2
- 150000002159 estradiols Chemical class 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000002657 hormone replacement therapy Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 2
- 229960004400 levonorgestrel Drugs 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- DNXXUUPUQXSUFH-UHFFFAOYSA-N neophyl chloride Chemical compound ClCC(C)(C)C1=CC=CC=C1 DNXXUUPUQXSUFH-UHFFFAOYSA-N 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- 239000000186 progesterone Substances 0.000 description 2
- 229960003387 progesterone Drugs 0.000 description 2
- 239000000044 progesterone antagonist Substances 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- WWYNJERNGUHSAO-XUDSTZEESA-N (+)-Norgestrel Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 WWYNJERNGUHSAO-XUDSTZEESA-N 0.000 description 1
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- PROQIPRRNZUXQM-UHFFFAOYSA-N (16alpha,17betaOH)-Estra-1,3,5(10)-triene-3,16,17-triol Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)O)C4C3CCC2=C1 PROQIPRRNZUXQM-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- OZHWXRNMIHHRCJ-UQCQJGFQSA-N (9r,10s,13r)-13-methyl-1,2,3,4,5,6,9,10,11,12-decahydrocyclopenta[a]phenanthrene-3-sulfonamide Chemical class C([C@@H]12)CC(S(N)(=O)=O)CC1CC=C1[C@@H]2CC[C@@]2(C)C1=CC=C2 OZHWXRNMIHHRCJ-UQCQJGFQSA-N 0.000 description 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- BXLRLFDGLUSGQD-UHFFFAOYSA-N 1-bromo-4,5-dimethyl-2-nitrobenzene Chemical group CC1=CC(Br)=C([N+]([O-])=O)C=C1C BXLRLFDGLUSGQD-UHFFFAOYSA-N 0.000 description 1
- SXVRSCIZJBGJGB-UHFFFAOYSA-N 1-chloropropan-2-ylbenzene Chemical compound ClCC(C)C1=CC=CC=C1 SXVRSCIZJBGJGB-UHFFFAOYSA-N 0.000 description 1
- VIPWUFMFHBIKQI-UHFFFAOYSA-N 1-fluoro-4-methoxybenzene Chemical compound COC1=CC=C(F)C=C1 VIPWUFMFHBIKQI-UHFFFAOYSA-N 0.000 description 1
- UHPDGGAYPGKHSG-UHFFFAOYSA-N 1-phenyl-5-(1-phenyltetrazol-5-yl)oxytetrazole Chemical compound N=1N=NN(C=2C=CC=CC=2)C=1OC1=NN=NN1C1=CC=CC=C1 UHPDGGAYPGKHSG-UHFFFAOYSA-N 0.000 description 1
- ZCECDJPMXUAMJE-UHFFFAOYSA-N 1-phenylcyclobutane-1-carbaldehyde Chemical compound C=1C=CC=CC=1C1(C=O)CCC1 ZCECDJPMXUAMJE-UHFFFAOYSA-N 0.000 description 1
- DHIDUDPFTZJPCQ-UHFFFAOYSA-N 1-phenylcyclobutane-1-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CCC1 DHIDUDPFTZJPCQ-UHFFFAOYSA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- JBKKAEOGAYZJCM-UHFFFAOYSA-N 2,1,3-benzoxadiazol-5-amine Chemical compound C1=C(N)C=CC2=NON=C21 JBKKAEOGAYZJCM-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- XBBMTLDJZXQHKN-UHFFFAOYSA-N 2,3-benzoxazin-1-one Chemical compound C1=CC=C2C(=O)ON=CC2=C1 XBBMTLDJZXQHKN-UHFFFAOYSA-N 0.000 description 1
- DWJKILXTMUGXOU-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetonitrile Chemical compound COC1=CC=CC=C1CC#N DWJKILXTMUGXOU-UHFFFAOYSA-N 0.000 description 1
- XQQYATDPOXGADN-UHFFFAOYSA-N 2-(trifluoromethyl)pentanoic acid Chemical compound CCCC(C(O)=O)C(F)(F)F XQQYATDPOXGADN-UHFFFAOYSA-N 0.000 description 1
- HRUFSRNDFLZZRI-UHFFFAOYSA-N 2-[ethylperoxy(hydroxy)phosphoryl]acetic acid Chemical compound CCOOP(O)(=O)CC(O)=O HRUFSRNDFLZZRI-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- ZPZZWEDXZBXDNZ-UHFFFAOYSA-N 2-hydroxy-4-(4-methoxy-3-nitrophenyl)-4-methyl-2-(trifluoromethyl)pentanoic acid Chemical compound COC1=CC=C(C(C)(C)CC(O)(C(O)=O)C(F)(F)F)C=C1[N+]([O-])=O ZPZZWEDXZBXDNZ-UHFFFAOYSA-N 0.000 description 1
- FTUIRGSMUVXOLJ-UHFFFAOYSA-N 2-hydroxy-4-methyl-4-phenyl-2-(trifluoromethyl)pentanoic acid Chemical compound OC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 FTUIRGSMUVXOLJ-UHFFFAOYSA-N 0.000 description 1
- WLTUFOLTUJPUBM-UHFFFAOYSA-N 2-hydroxy-n-(1-oxo-3h-2-benzofuran-5-yl)-4-phenyl-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)C1=CC=CC=C1 WLTUFOLTUJPUBM-UHFFFAOYSA-N 0.000 description 1
- SMGSCASLOXKZEW-UHFFFAOYSA-N 2-hydroxy-n-(3-methylbenzotriazol-5-yl)-4-phenyl-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2N=NN(C)C2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)C1=CC=CC=C1 SMGSCASLOXKZEW-UHFFFAOYSA-N 0.000 description 1
- DGODLUYLRNGXIK-UHFFFAOYSA-N 2-hydroxy-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-4-phenyl-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C(C(ON=C2C)=O)C2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)C1=CC=CC=C1 DGODLUYLRNGXIK-UHFFFAOYSA-N 0.000 description 1
- CJUROHVGRLRDPO-UHFFFAOYSA-N 2-hydroxy-n-[6-(3-hydroxy-3-methylbut-1-ynyl)-1-oxo-3h-2-benzofuran-5-yl]-4-methyl-4-phenyl-2-(trifluoromethyl)pentanamide Chemical compound CC(C)(O)C#CC1=CC=2C(=O)OCC=2C=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 CJUROHVGRLRDPO-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- XVTAQSGZOGYIEY-UHFFFAOYSA-N 3,4-dihydroisocoumarin Chemical compound C1=CC=C2C(=O)OCCC2=C1 XVTAQSGZOGYIEY-UHFFFAOYSA-N 0.000 description 1
- NTKIHVHEUWEYCW-UHFFFAOYSA-N 3-bromo-1,2-dimethyl-4-nitrobenzene Chemical group CC1=CC=C([N+]([O-])=O)C(Br)=C1C NTKIHVHEUWEYCW-UHFFFAOYSA-N 0.000 description 1
- ZMNLQWCUNRDBSL-UHFFFAOYSA-N 3-bromo-2-ethoxycarbonyl-4-nitrobenzoic acid Chemical class CCOC(=O)C1=C(Br)C([N+]([O-])=O)=CC=C1C(O)=O ZMNLQWCUNRDBSL-UHFFFAOYSA-N 0.000 description 1
- MBQRUNBMJUKYAB-UHFFFAOYSA-N 3-bromo-4-nitrophthalic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C(Br)=C1C(O)=O MBQRUNBMJUKYAB-UHFFFAOYSA-N 0.000 description 1
- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- ITYHTOVJGPCPTJ-UHFFFAOYSA-N 4-(2-iodophenyl)-4-methyl-2-oxopentanoic acid Chemical compound OC(=O)C(=O)CC(C)(C)C1=CC=CC=C1I ITYHTOVJGPCPTJ-UHFFFAOYSA-N 0.000 description 1
- HRLMPZYXEULDNM-UHFFFAOYSA-N 4-(3-bromo-4-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic acid Chemical compound COC1=CC=C(C(C)(C)CC(O)(C(O)=O)C(F)(F)F)C=C1Br HRLMPZYXEULDNM-UHFFFAOYSA-N 0.000 description 1
- KSWYPVXSQMQQCQ-UHFFFAOYSA-N 4-(3-bromophenyl)-4-methyl-2-oxopentanoic acid Chemical compound OC(=O)C(=O)CC(C)(C)C1=CC=CC(Br)=C1 KSWYPVXSQMQQCQ-UHFFFAOYSA-N 0.000 description 1
- OBYGOTQDJJKZHR-UHFFFAOYSA-N 4-(3-chlorophenyl)-4-methyl-2-oxopentanoic acid Chemical compound OC(=O)C(=O)CC(C)(C)C1=CC=CC(Cl)=C1 OBYGOTQDJJKZHR-UHFFFAOYSA-N 0.000 description 1
- FUZYBEBUPZRTMW-UHFFFAOYSA-N 4-(3-iodophenyl)-4-methyl-2-oxopentanoic acid Chemical compound OC(=O)C(=O)CC(C)(C)C1=CC=CC(I)=C1 FUZYBEBUPZRTMW-UHFFFAOYSA-N 0.000 description 1
- ZSGNXRBSOMVTIY-UHFFFAOYSA-N 4-(4-acetyl-3-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic acid Chemical compound COC1=CC(C(C)(C)CC(O)(C(O)=O)C(F)(F)F)=CC=C1C(C)=O ZSGNXRBSOMVTIY-UHFFFAOYSA-N 0.000 description 1
- LGMFTZSDDTYSFV-UHFFFAOYSA-N 4-(4-acetylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic acid Chemical compound CC(=O)C1=CC=C(C(C)(C)CC(O)(C(O)=O)C(F)(F)F)C=C1 LGMFTZSDDTYSFV-UHFFFAOYSA-N 0.000 description 1
- BXEFVIIFVYEQAZ-UHFFFAOYSA-N 4-(4-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic acid Chemical compound COC1=CC(Br)=CC=C1C(C)(C)CC(O)(C(O)=O)C(F)(F)F BXEFVIIFVYEQAZ-UHFFFAOYSA-N 0.000 description 1
- PXLGXUSMFYDZQH-UHFFFAOYSA-N 4-(4-bromo-2-methoxyphenyl)-4-methyl-2-oxopentanoic acid Chemical compound COC1=CC(Br)=CC=C1C(C)(C)CC(=O)C(O)=O PXLGXUSMFYDZQH-UHFFFAOYSA-N 0.000 description 1
- RUAHQASXJGQQQU-UHFFFAOYSA-N 4-(4-bromo-3-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic acid Chemical compound COC1=CC(C(C)(C)CC(O)(C(O)=O)C(F)(F)F)=CC=C1Br RUAHQASXJGQQQU-UHFFFAOYSA-N 0.000 description 1
- WZUBCFFJBUUCTE-UHFFFAOYSA-N 4-(4-bromophenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic acid Chemical compound OC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(Br)C=C1 WZUBCFFJBUUCTE-UHFFFAOYSA-N 0.000 description 1
- JGPFGHBCOHMIAU-UHFFFAOYSA-N 4-(4-carbamoylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic acid Chemical compound OC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(C(N)=O)C=C1 JGPFGHBCOHMIAU-UHFFFAOYSA-N 0.000 description 1
- SPKGOYRCPARZHO-UHFFFAOYSA-N 4-(4-cyano-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic acid Chemical compound COC1=CC(C#N)=CC=C1C(C)(C)CC(O)(C(O)=O)C(F)(F)F SPKGOYRCPARZHO-UHFFFAOYSA-N 0.000 description 1
- NDKYGTLERGKCEZ-UHFFFAOYSA-N 4-bromo-5-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)OC(=O)C2=C1Br NDKYGTLERGKCEZ-UHFFFAOYSA-N 0.000 description 1
- ZQUORFZTZDIZSU-UHFFFAOYSA-N 4-bromo-5-nitro-3h-2-benzofuran-1-one Chemical compound [O-][N+](=O)C1=CC=C2C(=O)OCC2=C1Br ZQUORFZTZDIZSU-UHFFFAOYSA-N 0.000 description 1
- UNJQBJIGSHGZAH-UHFFFAOYSA-N 4-bromo-5-nitrophthalic acid Chemical compound OC(=O)C1=CC(Br)=C([N+]([O-])=O)C=C1C(O)=O UNJQBJIGSHGZAH-UHFFFAOYSA-N 0.000 description 1
- BUHIMLPWWZRUEY-UHFFFAOYSA-N 4-ethyl-2,3-benzoxazin-1-one Chemical compound C1=CC=C2C(CC)=NOC(=O)C2=C1 BUHIMLPWWZRUEY-UHFFFAOYSA-N 0.000 description 1
- KKAZLRGZDIWYJT-UHFFFAOYSA-N 4-iodo-2-methoxybenzoic acid Chemical compound COC1=CC(I)=CC=C1C(O)=O KKAZLRGZDIWYJT-UHFFFAOYSA-N 0.000 description 1
- PDSZQDJIKVTPHU-UHFFFAOYSA-N 4-methyl-2,3-benzoxazin-1-one Chemical compound C1=CC=C2C(C)=NOC(=O)C2=C1 PDSZQDJIKVTPHU-UHFFFAOYSA-N 0.000 description 1
- FCUAFMSIYBZYLQ-UHFFFAOYSA-N 4-methyl-2-oxo-n-(1-oxo-3h-2-benzofuran-5-yl)-4-phenylpentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(=O)CC(C)(C)C1=CC=CC=C1 FCUAFMSIYBZYLQ-UHFFFAOYSA-N 0.000 description 1
- 239000001142 4-methyl-2-oxopentanoic acid Substances 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- OBBFRGLSKUBWLV-UHFFFAOYSA-N 5-[[2-hydroxy-4-phenyl-2-(trifluoromethyl)pentyl]amino]-3h-2-benzofuran-1-one Chemical compound C=1C=C2C(=O)OCC2=CC=1NCC(O)(C(F)(F)F)CC(C)C1=CC=CC=C1 OBBFRGLSKUBWLV-UHFFFAOYSA-N 0.000 description 1
- MYSWCVKZJGXLAG-UHFFFAOYSA-N 5-amino-3-prop-1-enyl-3h-2-benzofuran-1-one Chemical compound C1=C(N)C=C2C(C=CC)OC(=O)C2=C1 MYSWCVKZJGXLAG-UHFFFAOYSA-N 0.000 description 1
- KMAINKMYXGXMMX-UHFFFAOYSA-N 5-amino-6-bromo-3h-2-benzofuran-1-one Chemical compound C1=C(Br)C(N)=CC2=C1C(=O)OC2 KMAINKMYXGXMMX-UHFFFAOYSA-N 0.000 description 1
- DHELIGKVOGTMGF-UHFFFAOYSA-N 5-chloro-1-phenyltetrazole Chemical compound ClC1=NN=NN1C1=CC=CC=C1 DHELIGKVOGTMGF-UHFFFAOYSA-N 0.000 description 1
- JEONCVFTVUCPGE-UHFFFAOYSA-N 6-amino-4-methyl-2,3-benzoxazin-1-one Chemical compound C1=C(N)C=C2C(C)=NOC(=O)C2=C1 JEONCVFTVUCPGE-UHFFFAOYSA-N 0.000 description 1
- GBPLNDKPUHVINJ-UHFFFAOYSA-N 6-bromo-5-nitro-3h-2-benzofuran-1-one Chemical compound C1=C(Br)C([N+](=O)[O-])=CC2=C1C(=O)OC2 GBPLNDKPUHVINJ-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 241000456654 Acacia cana Species 0.000 description 1
- 240000005020 Acaciella glauca Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 206010006298 Breast pain Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 241000611750 Coregonus kiyi Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 206010013954 Dysphoria Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 208000007984 Female Infertility Diseases 0.000 description 1
- 206010016807 Fluid retention Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 108090000079 Glucocorticoid Receptors Proteins 0.000 description 1
- 102100033417 Glucocorticoid receptor Human genes 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000692870 Inachis io Species 0.000 description 1
- 206010021928 Infertility female Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000007466 Male Infertility Diseases 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 208000006662 Mastodynia Diseases 0.000 description 1
- 108090000375 Mineralocorticoid Receptors Proteins 0.000 description 1
- 102100021316 Mineralocorticoid receptor Human genes 0.000 description 1
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-Chlorosuccinimide Substances ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 102100025803 Progesterone receptor Human genes 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 235000013832 Valeriana officinalis Nutrition 0.000 description 1
- 244000126014 Valeriana officinalis Species 0.000 description 1
- FCVHBUFELUXTLR-UHFFFAOYSA-N [Li].[AlH3] Chemical compound [Li].[AlH3] FCVHBUFELUXTLR-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940030486 androgens Drugs 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229940124558 contraceptive agent Drugs 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
- AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 description 1
- UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 description 1
- 229960000978 cyproterone acetate Drugs 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 235000001159 dosh Nutrition 0.000 description 1
- 244000245171 dosh Species 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940096118 ella Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 239000003687 estradiol congener Substances 0.000 description 1
- 229960001348 estriol Drugs 0.000 description 1
- PROQIPRRNZUXQM-ZXXIGWHRSA-N estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 238000001794 hormone therapy Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FKUUDDGRDRPAQQ-UHFFFAOYSA-M magnesium;methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=C[C-]=C1 FKUUDDGRDRPAQQ-UHFFFAOYSA-M 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960002985 medroxyprogesterone acetate Drugs 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- XBLPTNDIRVYALA-UHFFFAOYSA-N n-(1-oxo-3h-2-benzofuran-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2C(=O)OCC2=C1 XBLPTNDIRVYALA-UHFFFAOYSA-N 0.000 description 1
- YMOWIYPUIBQBFF-UHFFFAOYSA-N n-(6-bromo-1-oxo-3h-2-benzofuran-5-yl)-4-methyl-2-oxo-4-phenylpentanamide Chemical compound C=1C=2COC(=O)C=2C=C(Br)C=1NC(=O)C(=O)CC(C)(C)C1=CC=CC=C1 YMOWIYPUIBQBFF-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- MIHJCLQINRFOLX-UHFFFAOYSA-N n-[4-nitro-3-(trifluoromethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MIHJCLQINRFOLX-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 229950006098 orthocaine Drugs 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005506 phthalide group Chemical group 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000468 progesterone receptors Proteins 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009256 replacement therapy Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/26—Androgens
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/34—Gestagens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/02—1,2-Oxazines; Hydrogenated 1,2-oxazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/76—Benzo[c]pyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Materials For Medical Uses (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19723722A DE19723722A1 (de) | 1997-05-30 | 1997-05-30 | Nichtsteroidale Gestagene |
PCT/EP1998/003242 WO1998054159A1 (fr) | 1997-05-30 | 1998-06-02 | Acylanilides non steroidiques heterocycliquement substitues a effet mixte gestagene et androgene |
Publications (1)
Publication Number | Publication Date |
---|---|
UA64752C2 true UA64752C2 (uk) | 2004-03-15 |
Family
ID=7831567
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA99127245A UA64752C2 (uk) | 1997-05-30 | 1998-02-06 | Нестероїдні (гетеро)циклічно заміщені ациланіліди з змішаною гестагенною та андрогенною активністю |
Country Status (30)
Country | Link |
---|---|
EP (1) | EP0986545B1 (fr) |
JP (1) | JP2002502385A (fr) |
KR (1) | KR100536870B1 (fr) |
CN (1) | CN100445272C (fr) |
AR (1) | AR011480A1 (fr) |
AT (1) | ATE286035T1 (fr) |
AU (1) | AU747083C (fr) |
BG (1) | BG64212B1 (fr) |
BR (1) | BR9809703A (fr) |
CA (1) | CA2305458C (fr) |
CZ (1) | CZ296377B6 (fr) |
DE (2) | DE19723722A1 (fr) |
EA (1) | EA004306B1 (fr) |
EE (1) | EE04492B1 (fr) |
ES (1) | ES2234121T3 (fr) |
HR (1) | HRP980289B1 (fr) |
HU (1) | HUP0002126A3 (fr) |
ID (1) | ID23499A (fr) |
IL (2) | IL133195A0 (fr) |
IS (1) | IS2498B (fr) |
NO (1) | NO325076B1 (fr) |
NZ (1) | NZ501359A (fr) |
PL (1) | PL197887B1 (fr) |
PT (1) | PT986545E (fr) |
SK (1) | SK284943B6 (fr) |
TR (1) | TR199902924T2 (fr) |
TW (1) | TW577882B (fr) |
UA (1) | UA64752C2 (fr) |
WO (1) | WO1998054159A1 (fr) |
ZA (1) | ZA984655B (fr) |
Families Citing this family (99)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19856475A1 (de) * | 1998-11-27 | 2000-05-31 | Schering Ag | Nichtsteroidale Entzündungshemmer |
DE10038639A1 (de) | 2000-07-28 | 2002-02-21 | Schering Ag | Nichtsteroidale Entzündungshemmer |
DE10346940B3 (de) * | 2003-10-06 | 2005-06-16 | Schering Ag | Substituierte Pentanole, ihre Verwendung zur Herstellung von Arzneimitteln speziell Entzündungshemmer sowie diese enthaltende pharmazeutische Präparate |
EP1373888A2 (fr) * | 2000-12-28 | 2004-01-02 | Schering Aktiengesellschaft | Procede de criblage de ligands a specificite pour l'isoforme des recepteurs de progesterone |
WO2003059899A1 (fr) * | 2002-01-14 | 2003-07-24 | Boehringer Ingelheim Pharmaceuticals, Inc. | Mimetiques de glucocorticoides, procedes de fabrication, preparations pharmaceutiques renfermant ces mimetiques et utilisations |
DK1482925T3 (da) * | 2002-03-11 | 2007-05-14 | Bayer Schering Pharma Ag | 5- (2-hydroxy-3 -'1 - (3-trifluormethylphenyl) cyclopropylpropionylamino) phtalid og relaterede forbindelser med progesteronreceptormoducerende aktivitet til anvendelse i fertilitetskontrol og hormonerstatningsterapi |
EP1344776A1 (fr) * | 2002-03-11 | 2003-09-17 | Schering Aktiengesellschaft | Dérivés de la 5- 2-hydroxy-3-[1-(3-trifluorométhylphényl)-cyclopropyl]-propionylamino -phtalide et de la 6- 2-hydroxy-3-[1-(3-trifluoromethylphenyl)-cyclopropyl]-propionylamino -4-methyl-2,3-benzoxazin-1-one avec une activité modulante du recepteur de la progesterone pour l'utilisation dans la contraception , la therapie du remplacement hormonell et le traitement des troubles gynécologiques |
AU2003230700A1 (en) | 2002-03-26 | 2003-10-13 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
UA80120C2 (en) | 2002-03-26 | 2007-08-27 | Boehringer Ingelheim Pharma | Glucocorticoid mimetics, pharmaceutical composition based thereon |
DE10215316C1 (de) * | 2002-04-02 | 2003-12-18 | Schering Ag | Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als Entzündungshemmer |
US7186864B2 (en) | 2002-05-29 | 2007-03-06 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
US7074806B2 (en) | 2002-06-06 | 2006-07-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
CA2496175A1 (fr) | 2002-08-21 | 2004-03-04 | Boehringer Ingelheim Pharmaceuticals, Inc. | Composes mimetiques de glucocorticoide, leurs procedes de fabrication, compositions pharmaceutiques, et leurs utilisations |
MXPA05002297A (es) | 2002-08-29 | 2005-06-08 | Boehringer Ingelheim Pharma | Derivados-3(sulfoamidoetil)-indol para uso como compuestos mimeticos de glucocorticoides en el tratamiento de enfermedades inflamatorias, alergicas y proliferativas. |
WO2004035737A2 (fr) * | 2002-10-15 | 2004-04-29 | University Of Tennessee Research Foundation | Modulateurs heterocycliques selectifs du recepteur des androgenes et procedes d'utilisation associes |
DE10261874A1 (de) * | 2002-12-20 | 2004-07-08 | Schering Ag | Nichtsteroidale Entzündungshemmer |
US7579469B2 (en) | 2003-01-03 | 2009-08-25 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
US20040224992A1 (en) * | 2003-02-27 | 2004-11-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
KR20060027376A (ko) * | 2003-07-01 | 2006-03-27 | 쉐링 악티엔게젤샤프트 | 헤테로시클릭 치환된 펜탄올 유도체, 그의 제조 방법 및그의 항염증제로서 용도 |
GB0316290D0 (en) | 2003-07-11 | 2003-08-13 | Glaxo Group Ltd | Novel compounds |
UY28526A1 (es) | 2003-09-24 | 2005-04-29 | Boehringer Ingelheim Pharma | Miméticos de glucocorticoides, métodos de preparación composiciones farmacéuticas y usos de los mismos |
ATE366726T1 (de) | 2003-10-16 | 2007-08-15 | Boehringer Ingelheim Pharma | Stereoselektive synthese bestimmter trifluormethylsubstituierter alkohole |
US7795272B2 (en) | 2004-03-13 | 2010-09-14 | Boehringer Ingelheim Pharmaceutical, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof |
PE20060272A1 (es) | 2004-05-24 | 2006-05-22 | Glaxo Group Ltd | (2r,3r,4s,5r,2'r,3'r,4's,5's)-2,2'-{trans-1,4-ciclohexanodiilbis-[imino(2-{[2-(1-metil-1h-imidazol-4-il)etil]amino}-9h-purin-6,9-diil)]}bis[5-(2-etil-2h-tetrazol-5-il)tetrahidro-3,4-furanodiol] como agonista a2a |
TWI307630B (en) | 2004-07-01 | 2009-03-21 | Glaxo Group Ltd | Immunoglobulins |
DE102004062182B4 (de) * | 2004-12-20 | 2007-06-06 | Bayer Schering Pharma Ag | Transdermales Pflaster mit Progesteron A-Spezifische Liganden (PRASL) als Wirkstoff |
ATE433958T1 (de) | 2004-12-27 | 2009-07-15 | Boehringer Ingelheim Pharma | Glucocorticoid-mimetika, verfahren zu deren herstellung, pharmazeutische zusammensetzungen und deren verwendung |
WO2006072599A2 (fr) | 2005-01-10 | 2006-07-13 | Glaxo Group Limited | Nouveaux composes |
WO2006083030A1 (fr) * | 2005-02-04 | 2006-08-10 | Ajinomoto Co., Inc. | Procédé servant à produire un acide gras et sel ou cristaux d'un acide gras |
UY29439A1 (es) | 2005-03-25 | 2006-10-02 | Glaxo Group Ltd | Nuevos compuestos |
AR053346A1 (es) | 2005-03-25 | 2007-05-02 | Glaxo Group Ltd | Compuesto derivado de 8h -pirido (2,3-d) pirimidin -7 ona 2,4,8- trisustituida composicion farmaceutica y uso para preparar una composicion para tratamiento y profilxis de una enfermedad mediada por la quinasa csbp/ rk/p38 |
DE102005017326A1 (de) * | 2005-04-14 | 2007-03-29 | Schering Ag | Tetrahydronaphthalinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
US7408060B2 (en) | 2005-06-24 | 2008-08-05 | Schering Ag | Nonsteroidal progesterone receptor modulators |
DE102005030293A1 (de) * | 2005-06-24 | 2007-01-04 | Schering Ag | Verwendung von nichtsteroidale Progesteronrezeptor-Modulatoren |
DE102005030294A1 (de) * | 2005-06-24 | 2007-01-04 | Schering Ag | Nichtsteroidale Progesteronrezeptor-Modulatoren |
GB0514809D0 (en) | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
BRPI0619518A2 (pt) | 2005-12-09 | 2011-10-11 | Hoffmann La Roche | moduladores do receptor de glicocorticoide, composição farmacêutica que os compreende e usos dos mesmos |
PE20071068A1 (es) | 2005-12-20 | 2007-12-13 | Glaxo Group Ltd | Acido 3-(4-{[4-(4-{[3-(3,3-dimetil-1-piperidinil)propil]oxi}fenil)-1-piperidinil]carbonil}-1-naftalenil)propanoico o propenoico, sales de los mismos, como antagonistas de los receptores h1 y h3 |
MX2008013411A (es) | 2006-04-20 | 2008-11-04 | Glaxo Group Ltd | Nuevos compuestos. |
GB0611587D0 (en) | 2006-06-12 | 2006-07-19 | Glaxo Group Ltd | Novel compounds |
BRPI0720131A2 (pt) | 2006-12-06 | 2014-02-04 | Boehringer Ingelheim Int | Glicocorticoides miméticos, métodos para fazê-los, composições farmacêuticas e usos dos mesmos. |
DE102007023614A1 (de) | 2007-05-21 | 2008-11-27 | Bayer Schering Pharma Aktiengesellschaft | Nichtsteroidale Progesteronrezeptor-Modulatoren |
UY30805A1 (es) * | 2006-12-21 | 2008-07-31 | Bayer Schering Pharma Ag | Moduladores no esteroides de receptores de progesterona |
DE102007049630A1 (de) | 2007-10-11 | 2009-10-29 | Bayer Schering Pharma Aktiengesellschaft | Nichtsteroidale Progesteronrezeptor-Modulatoren |
UY30815A1 (es) * | 2006-12-21 | 2008-07-31 | Bayer Schering Pharma Ag | Moduladores no esteroidales del receptor de progesterona |
JP5090773B2 (ja) | 2006-12-26 | 2012-12-05 | 国立大学法人東京工業大学 | 光学活性含フッ素カルボニル−エン生成物の製造方法 |
PE20081889A1 (es) | 2007-03-23 | 2009-03-05 | Smithkline Beecham Corp | Indol carboxamidas como inhibidores de ikk2 |
DE102007032800A1 (de) | 2007-07-10 | 2009-01-15 | Bayer Schering Pharma Aktiengesellschaft | Nichtsteroidale Progesteronrezeptor-Modulatoren |
DE102007058747A1 (de) | 2007-12-05 | 2009-06-10 | Bayer Schering Pharma Aktiengesellschaft | Nichtsteroidale Progesteronrezeptor-Modulatoren |
EP2070909A1 (fr) * | 2007-12-15 | 2009-06-17 | Bayer Schering Pharma AG | Modulateurs de récepteur de progestérone non stéroïdiens |
BRPI0912267A2 (pt) | 2008-05-23 | 2015-10-13 | Amira Pharmaceuticals Inc | sal farmaceuticamente aceitável, composição farmacêutica, artigo de fabricação, métodos para tratar asma, rinite alérgica, doença, lesões gástricas e dor, métodos para prevenir broncoconstrição e rinite alérgica, uso de um sal farmaceuticamente aceitável, e, processo para a preparação de um sal farmaceuticamente aceitável. |
ES2383246T3 (es) | 2008-06-05 | 2012-06-19 | Glaxo Group Limited | 4-amino-indazoles |
WO2009147187A1 (fr) | 2008-06-05 | 2009-12-10 | Glaxo Group Limited | Dérivés de 4-carboxamide indazole utiles en tant qu'inhibiteurs de p13 kinases |
DK2300472T3 (da) | 2008-06-06 | 2012-04-10 | Boehringer Ingelheim Int | Glucocorticoidmimetika, fremgangsmåder til disses fremstilling, farmaceutiske sammensætninger samt anvendelser deraf |
WO2010094643A1 (fr) | 2009-02-17 | 2010-08-26 | Glaxo Group Limited | Dérivés de quinoline et applications associées dans la rhinite et l'urticaire |
US8524751B2 (en) | 2009-03-09 | 2013-09-03 | GlaxoSmithKline Intellecutual Property Development | 4-oxadiazol-2-YL-indazoles as inhibitors of P13 kinases |
WO2010102968A1 (fr) | 2009-03-10 | 2010-09-16 | Glaxo Group Limited | Dérivés d'indole comme inhibiteurs de ikk2 |
EP2408769A1 (fr) | 2009-03-17 | 2012-01-25 | Glaxo Group Limited | Dérivés de pyrimidine utilisés comme inhibiteurs de ltk |
EP2408458A1 (fr) | 2009-03-19 | 2012-01-25 | Merck Sharp&Dohme Corp. | INHIBITION INDUITE PAR ARN INTERFÉRENCE DE L'EXPRESSION DU GÈNE TRANSDUCTEUR DE SIGNAL ET ACTIVITATEUR DE TRANSCRIPTION 6 (STAT6) AU MOYEN D'UN ACIDE NUCLÉIQUE INTERFÉRENT COURT (ANsi) |
US20120016011A1 (en) | 2009-03-19 | 2012-01-19 | Merck Sharp & Dohme Corp. | RNA Interference Mediated Inhibition of Connective Tissue Growth Factor (CTGF) Gene Expression Using Short Interfering Nucleic Acid (siNA) |
CN102439151A (zh) | 2009-03-19 | 2012-05-02 | 默沙东公司 | 使用短干扰核酸(siNA)的RNA干扰介导的BTB和CNC同系物1,碱性亮氨酸拉链转录因子1(Bach1)基因表达的抑制 |
JP2012520685A (ja) | 2009-03-19 | 2012-09-10 | メルク・シャープ・エンド・ドーム・コーポレイション | 低分子干渉核酸(siNA)を用いたGATA結合タンパク質3(GATA3)遺伝子発現のRNA干渉媒介性阻害 |
JP2012521764A (ja) | 2009-03-27 | 2012-09-20 | メルク・シャープ・エンド・ドーム・コーポレイション | 低分子干渉核酸(siNA)を用いた胸腺間質性リンパ球新生因子(TSLP)遺伝子発現のRNA干渉媒介性阻害 |
WO2010111497A2 (fr) | 2009-03-27 | 2010-09-30 | Merck Sharp & Dohme Corp. | Inhibition à médiation par l'interférence arn de l'expression du gène de la molécule d'adhésion intercellulaire 1 (icam-1) faisant appel à de courts acides nucléiques interférents (ansi) |
WO2010111468A2 (fr) | 2009-03-27 | 2010-09-30 | Merck Sharp & Dohme Corp. | INHIBITION PAR INTERFÉRENCE ARN DE L'EXPRESSION DU GÈNE DE LA CHAÎNE BÊTA DU FACTEUR DE CROISSANCE DES NERFS (NGFß) AU MOYEN D'UN ACIDE NUCLÉIQUE INTERFÉRENT COURT (ANSI) |
WO2010111464A1 (fr) | 2009-03-27 | 2010-09-30 | Merck Sharp & Dohme Corp. | Inhibition par interférence arn de l'expression du gène kinase 1 de régulation du signal d'apoptose (ask1) au moyen d'un acide nucléique interférent court (ansi) |
EP2411019A2 (fr) | 2009-03-27 | 2012-02-01 | Merck Sharp&Dohme Corp. | Inhibition par interférence arn de l'expression du gène du signal transducteur et activateur de la transcription 1 (stat1) au moyen d'un acide nucléique interférent court (ansi) |
WO2010122088A1 (fr) | 2009-04-24 | 2010-10-28 | Glaxo Group Limited | Pyrazole et triazole carboxamides en tant qu'inhibiteurs du canal crac |
JP2012524755A (ja) | 2009-04-24 | 2012-10-18 | グラクソ グループ リミテッド | Cracチャネル阻害剤としてのn−ピラゾリルカルボキサミド |
US8575162B2 (en) | 2009-04-30 | 2013-11-05 | Glaxosmithkline Intellectual Property Development Limited | Compounds |
WO2011067366A1 (fr) | 2009-12-03 | 2011-06-09 | Glaxo Group Limited | Dérivés d'indazole comme inhibiteurs des pi3-kinases |
JP2013512879A (ja) | 2009-12-03 | 2013-04-18 | グラクソ グループ リミテッド | Pi3キナーゼの阻害剤としてのベンズピラゾール誘導体 |
EP2507226A1 (fr) | 2009-12-03 | 2012-10-10 | Glaxo Group Limited | Nouveaux composés |
EP2512438B1 (fr) | 2009-12-16 | 2017-01-25 | 3M Innovative Properties Company | Formulations et procédés pour le réglage de l'administration de particules d'une certaine taille dans un aérosol-doseur |
WO2011110575A1 (fr) | 2010-03-11 | 2011-09-15 | Glaxo Group Limited | Dérivés de 2-[2-(benzo- ou pyrido-)thiazolylamino]-6- aminopyridine, utiles dans le traitement de maladies respiratoires, allergiques ou inflammatoires |
GB201007203D0 (en) | 2010-04-29 | 2010-06-16 | Glaxo Group Ltd | Novel compounds |
WO2012032065A1 (fr) | 2010-09-08 | 2012-03-15 | Glaxo Group Limited | Dérivés indazole à utiliser dans le traitement d'une infection par le virus de la grippe |
HUE026059T2 (en) | 2010-09-08 | 2016-05-30 | Glaxosmithkline Ip Dev Ltd | N- [5- [4- (5 - {[(2R, 6S) -2,6-dimethyl-4-morpholinyl] methyl} -1,3-oxazol-2-yl) -1H-indazol-6-yl ] Polymorphs and salts of 2 - (methyloxy) -3-pyridinyl] methanesulfonamide |
WO2012035055A1 (fr) | 2010-09-17 | 2012-03-22 | Glaxo Group Limited | Nouveaux composés |
WO2012052458A1 (fr) | 2010-10-21 | 2012-04-26 | Glaxo Group Limited | Composés pyrazole agissant contre des états allergiques, immunitaires et inflammatoires |
JP2013544794A (ja) | 2010-10-21 | 2013-12-19 | グラクソ グループ リミテッド | アレルギー性障害、炎症性障害及び免疫障害に作用するピラゾール化合物 |
GB201018124D0 (en) | 2010-10-27 | 2010-12-08 | Glaxo Group Ltd | Polymorphs and salts |
GB201104153D0 (en) | 2011-03-11 | 2011-04-27 | Glaxo Group Ltd | Novel compounds |
WO2012123312A1 (fr) | 2011-03-11 | 2012-09-20 | Glaxo Group Limited | Dérivés pyrido[3,4-b]pyrazine en tant qu'inhibiteurs de syk |
MY184292A (en) | 2013-09-22 | 2021-03-30 | Sunshine Lake Pharma Co Ltd | Substituted aminopyrimidine compounds and methods of use |
CA2925064A1 (fr) | 2013-10-17 | 2015-04-23 | Glaxosmithkline Intellectual Property Development Limited | Inhibiteur de pi3k pour le traitement d'une maladie respiratoire |
US20160256466A1 (en) | 2013-10-17 | 2016-09-08 | Glaxosmithkline Intellectual Property Development Limited | Pi3k inhibitor for treatment of respiratory disease |
WO2015148867A1 (fr) | 2014-03-28 | 2015-10-01 | Calitor Sciences, Llc | Composés hétéroaryle substitués et procédés d'utilisation |
SG11201609276RA (en) | 2014-05-12 | 2016-12-29 | Glaxosmithkline Ip No 2 Ltd | Pharmaceutical compositions comprising danirixin for treating infectious diseases |
EP3347097B1 (fr) | 2015-09-11 | 2021-02-24 | Sunshine Lake Pharma Co., Ltd. | Dérivés d' aminopyrimidine substitués en tant que modulateurs des kinases jak, flt3 et aurora |
GB201602527D0 (en) | 2016-02-12 | 2016-03-30 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
WO2018029126A1 (fr) | 2016-08-08 | 2018-02-15 | Glaxosmithkline Intellectual Property Development Limited | Composés chimiques |
GB201706102D0 (en) | 2017-04-18 | 2017-05-31 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
GB201712081D0 (en) | 2017-07-27 | 2017-09-13 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
EP3569228A1 (fr) * | 2018-05-17 | 2019-11-20 | Association pour la recherche à l'IGBMC (ARI) | Modulateurs agonistes de récepteurs de glucocorticoïdes sélectifs (segrams) non stéroïdiens et leurs utilisations |
WO2019099311A1 (fr) | 2017-11-19 | 2019-05-23 | Sunshine Lake Pharma Co., Ltd. | Composés hétéroaryle substitués et leurs méthodes d'utilisation |
EP3740468A4 (fr) | 2018-01-20 | 2021-10-06 | Sunshine Lake Pharma Co., Ltd. | Composés d'aminopyrimidine substitués et procédés d'utilisation |
JP2023519585A (ja) | 2020-03-26 | 2023-05-11 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッド | ウイルス感染を予防または治療するカテプシン阻害剤 |
CN114605308B (zh) * | 2022-03-18 | 2023-12-19 | 阜新孚隆宝医药科技有限公司 | 一种帕罗韦德的氮杂双环医药中间体的制备方法及中间体 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4191775A (en) * | 1977-12-15 | 1980-03-04 | Imperial Chemical Industries Limited | Amide derivatives |
NZ197008A (en) * | 1980-05-22 | 1984-10-19 | Ici Ltd | Acylanilide derivatives and pharmaceutical compositions |
JPS5789048A (en) * | 1980-11-20 | 1982-06-03 | Nat Jutaku Kenzai | Independent pilar with cover |
CA1261835A (fr) * | 1984-08-20 | 1989-09-26 | Masaaki Toda | Benz(thio) amides fusionnes |
GB8617652D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Acylanilide derivatives |
GB8617653D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Amide derivatives |
AU668206B2 (en) * | 1992-07-01 | 1996-04-26 | Ortho Pharmaceutical Corporation | 1-arylsulphonyl, arylcarbonyl and 1-arylphosphonyl-3-phenyl-1,4,5,6-tetrahydropyridazines |
-
1997
- 1997-05-30 DE DE19723722A patent/DE19723722A1/de not_active Ceased
-
1998
- 1998-02-06 UA UA99127245A patent/UA64752C2/uk unknown
- 1998-05-29 ZA ZA984655A patent/ZA984655B/xx unknown
- 1998-05-29 HR HR980289A patent/HRP980289B1/xx not_active IP Right Cessation
- 1998-06-01 AR ARP980102552A patent/AR011480A1/es active IP Right Grant
- 1998-06-01 TW TW087108524A patent/TW577882B/zh not_active IP Right Cessation
- 1998-06-02 IL IL13319598A patent/IL133195A0/xx active IP Right Grant
- 1998-06-02 HU HU0002126A patent/HUP0002126A3/hu unknown
- 1998-06-02 CN CNB98805597XA patent/CN100445272C/zh not_active Expired - Fee Related
- 1998-06-02 ID IDW991498A patent/ID23499A/id unknown
- 1998-06-02 ES ES98928338T patent/ES2234121T3/es not_active Expired - Lifetime
- 1998-06-02 PL PL337088A patent/PL197887B1/pl unknown
- 1998-06-02 EE EEP199900548A patent/EE04492B1/xx not_active IP Right Cessation
- 1998-06-02 BR BR9809703-2A patent/BR9809703A/pt not_active IP Right Cessation
- 1998-06-02 EA EA199900989A patent/EA004306B1/ru not_active IP Right Cessation
- 1998-06-02 TR TR1999/02924T patent/TR199902924T2/xx unknown
- 1998-06-02 NZ NZ501359A patent/NZ501359A/en unknown
- 1998-06-02 AT AT98928338T patent/ATE286035T1/de not_active IP Right Cessation
- 1998-06-02 PT PT98928338T patent/PT986545E/pt unknown
- 1998-06-02 KR KR10-1999-7011103A patent/KR100536870B1/ko not_active IP Right Cessation
- 1998-06-02 WO PCT/EP1998/003242 patent/WO1998054159A1/fr active IP Right Grant
- 1998-06-02 JP JP50026799A patent/JP2002502385A/ja not_active Ceased
- 1998-06-02 EP EP98928338A patent/EP0986545B1/fr not_active Expired - Lifetime
- 1998-06-02 DE DE59812452T patent/DE59812452D1/de not_active Expired - Fee Related
- 1998-06-02 CZ CZ0425799A patent/CZ296377B6/cs not_active IP Right Cessation
- 1998-06-02 CA CA002305458A patent/CA2305458C/fr not_active Expired - Fee Related
- 1998-06-02 SK SK1609-99A patent/SK284943B6/sk not_active IP Right Cessation
- 1998-06-02 AU AU80211/98A patent/AU747083C/en not_active Ceased
-
1999
- 1999-11-09 IS IS5241A patent/IS2498B/is unknown
- 1999-11-19 BG BG103903A patent/BG64212B1/bg unknown
- 1999-11-29 NO NO19995845A patent/NO325076B1/no unknown
- 1999-11-29 IL IL133195A patent/IL133195A/en not_active IP Right Cessation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
UA64752C2 (uk) | Нестероїдні (гетеро)циклічно заміщені ациланіліди з змішаною гестагенною та андрогенною активністю | |
US6344454B1 (en) | Nonsteroidal gestagens | |
US20090099250A1 (en) | Benzocycloheptene derivatives as estrogens having selective activity | |
FR2534582A1 (fr) | Nouveaux derives de benzofuranne et de benzothiophene, utiles comme agents anti-hyperuricemie et anti-hypertension, et leur procede de fabrication | |
CA1140110A (fr) | Procede de preparation de nouveaux derives de l'androst-4-ene | |
Gauthier et al. | New Highly Stereoselective Synthesis of (E)-Droloxifene via Selective Protection of 3, 4′-Dihydroxybenzophenone and McMurry Reaction | |
JPS6156146A (ja) | 大環状ケトンの製造方法 | |
CA2013322A1 (fr) | Derives d'acyl-5 benzoxazolinone, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent | |
CA1100527A (fr) | Derives de l'acide cyclohexyl-4 naphtalene acetique-1, procede d'obtention et application a titre de medicament | |
JPH0720951B2 (ja) | チオフェン酢酸の新誘導体、それらの製造法及び薬剤としての使用 | |
BE715778A (fr) | ||
CH345887A (fr) | Procédé de préparation de dérivés de la 1-déhydro-adrénostérone | |
CH363978A (fr) | Procédé pour la préparation de l'a-estradiol | |
BE598605A (en) | Alkenylamines and pharmaceutical preparations containing them | |
BE665139A (fr) | ||
CH511253A (fr) | Procédé de préparation de nouveaux dérivés 2-oxa-stéroïdes insaturés | |
NO750579L (fr) | ||
BE715663A (fr) | ||
FR2534583A1 (fr) | Procede pour la fabrication d'hexahydro-5-hydroxy-4-hydroxymethyl-2h-cyclopenta-(b)-furanne-2-one | |
CH285626A (fr) | Procédé pour la préparation d'un nouveau dérivé de l'oestradiol. | |
BE461458A (fr) |